


Brothers and Best Friends

by WeezieMcSqueezie



Category: Supernatural
Genre: BFFs, Eventual Smut, F/M, FEELINGS ARE WEIRD, Fluff and Mush, Friends With Benefits, Jealousy, Romantic Fluff, besties, dean winchester is a jerk
Language: English
Status: Completed
Published: 2021-03-13
Updated: 2021-03-22
Packaged: 2021-03-21 16:07:48
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 7,399
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30024333
Author URL: https://archiveofourown.org/users/WeezieMcSqueezie/pseuds/WeezieMcSqueezie
Summary: This series explores Dean and Holly falling in love while her best friend comes to visit.
Relationships: Dean Winchester and Holly, Dean Winchester/Original Female Character(s), Sam Winchester & Josie, Sam Winchester & Original Female Character(s)
Comments: 3
Kudos: 3





	1. Feels are Weird

**Author's Note:**

> I've renamed this since it looks like it's turning into a series.
> 
> Chapter 1 is all about Dean being a dumbass and trying to fix it.

It’s been a week since he’s seen Holly. He misses her but he won’t admit that. He wants to keep things cool with them, noncommittal. She and Charlie went off for a girls weekend after they'd finished their hunt a few days ago. Glamping or some shit he didn’t understand. Didn’t care, really, just wanted her back. She’d texted him asking for his famous burgers for dinner and of course he would cook for her. He’d do anything for her, except admit how he really feels. 

He pulls on his pants and shoes to make a grocery run. He hears her voice floating down the hall from Sam’s room. She’s home? He thought she’d texted from the road. I don’t want to wake Dean” he heard her say as she hissed in pain. “No problem. I’ve got plenty. It’ll feel good once I rub it in. Supposed to be amazing for your skin. You really need to use protection every time, though” Sam said. What the fuck was going on in there? He approached the door, which was mostly closed and heard her say, “Sam! Careful! You’re squirting on my shirt!” “Stop moving and I’ll keep it on your face!” Sam said, mild annoyance in his voice. Dean pushed the door open and he saw the back of Sam, standing at the side of his bed, her legs sticking out between his from where she sat. “Ewe…it’s in my hair now” she sighed.

“What the fuck?” he said and Sam turned to look over his shoulder. “Hey, Dean” Sam said and turned back to Holly. Dean lunged at Sam and threw him into the dresser. “DEAN!” she shrieked and when he looked at her, she was sitting the in a tank top and heavily sunburned holding a bottle of aloe in her hands. “DUDE! What the fuck, man!” Sam shouted and pushed off the dresser stepping into Dean’s face. “What is this?” Dean looked between the two of them, already knowing he’d made a total ass out of himself, but still too angry to care much. “I’m fried to a crisp and didn’t want to wake you for help getting my back!” she shouted, eyes livid. “And your face? Can’t do that yourself?” he hated myself the moment the words left my mouth. He watched her back stiffen and knew he’d dug himself into a nice, deep hole. “Dude, you’re WAY out of line. Get the fuck out of this room. Right now!” Sam roared at him. He flashed him a look then flicked his eyes back to her before storming out. 

He managed to make it through the market without scaring anyone too badly with his sour mood. He came back to find then in the library working on cataloguing some shit or other. Sam looked up and in the special that only two people who have been to war together can manage, they had a silent conversation and Sam nodded his acceptance of the apology. Sam flicked his eyes to Holly and Dean knew that was going to be an incredibly uphill battle and walked through to the kitchen to start dinner. 

He made bacon cheeseburgers, fries and a salad that he made manly with a bacon vinaigrette he saw on Pinterest, though he’d deny ever having a Pinterest account. Cas showed up, which helped break up the uncomfortable silence Holly was throwing his way. Cas followed him back into the kitchen and helped with the dishes. “I’m sensing Holly is upset with you” Cas said in obvious and deadpan manner that is uniquely Cas. “You’re not kidding” Dean sighed and set the last dish on the drying rack. “I rarely kid, Dean” Cas said. Smiling Dean turned to his friend and slapped his shoulder. “Don’t ever change, man. I’m gonna go try to fix this” Dean said and hung the towel on the edge of the sink.

He found her in her bedroom pulling off her shoes and socks. She knew he was there, but didn’t acknowledge him. A quick survey of the room and he spotted her bathtub kit and robe on the bed. A plan quickly formulated, and he left her to change into her robe. “Sam, where is my hovercraft?” he asked running into the library. “Uh, garage, I think. Your toys, Dean. You gotta keep track of them” Sam laughed. “Thanks. Uh, nobody needs the shower room, right?” he looked between Sam and Cas. “I don’t need to shower” Cas said and Sam shook his head, “I’m good.” He smiled and ran into the map room and grabbed on of her extra cell phones. “What are you doing?” Sam asked. “Fixing my mistakes, man” he said and took off down the hall. “How can he make her happy with a flying toy?” Cas asked and Sam shrugged. 

He found the hovercraft and tied her phone to hit and turned everything on for a test run. “Perfect!” he grinned and set off to the shower room. He heard the water running and crept in, hiding himself behind a shower curtain. He watched her sink into the water and waited until she turned the tap off and settled back. He floated the phone across the room and when she heard the motor, her eyes flew open and her fight face activated. He grinned, knowing she had a knife hidden in her tub kit after having seen too many horror movies and but when she relaxed again he thought maybe he had a chance. He maneuvered it over the tub so that it floated in front of her face an set the machine to hold it’s place. 

He pulled out his phone and sent off the first in a series of texts. _Feelings make me feel weird. You give me feelings. You make me feel weird._ She rolled her eyes. Okay, not bad, he thought. _I am sorry for being an asshole._ _I was jealous of what I thought was happening in Sam’s room._ She rolled her eyes again. _I know we aren’t in a relationship and that you have the right to be with anyone you want to be with_. She snorted picking up her wine for a long sip. _I want you to be with me. Only me. Because you make me feel the weird things._ She sat up a little straighter. _I want you to be my girl. Because I’m selfish. Because I want to feel the weird things with you._ He waited a beat and sent the last message. _Do you want that too?_ He watched her hand hover over the phone, but he couldn’t see what she’d typed. Then, a message popped up on his phone. _Yes_. 

He let out the breath he didn’t know he was holding and flew the hovercraft towards him as he stepped out of the shower. She was resting back with her eyes closed when he approached. He knelt beside the tub and stroked her face. When their eyes met, he knew he felt way more than just the weird things and he was going to have to figure out how to deal with that. For how, though, he just wanted to be with her in this moment. The rest would come later. 


	2. Holly's Confession

**Summary for the Chapter:**

> Holly's friend will come to visit her at the bunker soon and she tells Dean about their past. He likes what he hears.

They were crowded into the tiny security room at the nursing home. They’d all applied for the job but Sam was ultimately hired as the night security officer and snuck them in. The room was the size of a walk-in closet with a desk taking up one wall, filing cabinets along the other and at the far end opposite the door was a narrow window. Sam was sitting in the only chair reviewing the footage from the last 24-hours while Holly kept an eye on the current feeds. “C’mere” Dean said after about thirty minutes and pulled her to him as he sat on the deep windowsill. She allowed herself to be handled and he settled her against his chest so that her butt rested against his incredibly impressive erection. Dean wrapped his arms around her waist and tucked his face into her neck. Within minutes he was snoring lightly, his boner fading. Sam looked over and shook his head. “I know. His ability to sleep anywhere at anytime is impressive” she laughed. 

After a week of hard work, they found the shifter a few hours later, the eye-flare on the screen giving it up. Dean wanted to deal with it immediately, but he was outvoted so they tracked it until the end of its shift and followed it home. Better to do it away from security cameras, was Holly’s reasoning. Back at the motel Dean asked, “When is your friend coming? We can trust her with the bunker’s location and all?” Holly nodded, “Next week and yes, Dean. I wouldn’t bring anyone around who couldn’t be trusted. We’ve been over this.” Sam said, “I’m going to take a shower. Please get your argument out of the way before I finish up.” Dean laughed as Sam closed the bathroom door. 

“Um, there’s something I should tell you about Josie” Holly said and sat on Dean’s lap at the table. She palmed the beer from his hand and took a long sip. “What’s that?” he asked taking back the beer. “She and I used to fuck” she said making Dean almost spit out the swallow of beer. He sputtered a minute and then said, “Wanna give me details on that?” She laughed, the sound always magical to his ears, “When we hunted together, sometimes we’d fool around. Was fun. I just thought you should know so that it’s out in the open.” He nodded slowly and she saw the wheels spinning in his head. “Dean. This does not mean you’re scoring a threesome, so get that idea out of your head” she warned. “Yeah, but, have you tried a threesome?” he asked. “No and I’m not planning on sharing you” she kissed his nose and stood up. Dean sighed, dejected but not entirely hopeless, “What if I just watch?” She shook her head, “Look, I told you so that there was complete honesty here not so you could perv out.” He threw her one of Sam’s epic bitchfaces, “Having a healthy imagination and strong sex drive doesn’t make me a perv. Besides, you like pervy shit.” 

Ten minutes later Sam came out, steam billowing out of the bathroom behind him. “Hey Sammy! Holly and her friend Josie used to be lesbians together” he grinned broadly. “DEAN!” Holly whirled on him throwing her belt across the room at him. He caught it with ease as Sam said, “Uh, that’s great Dean, but doesn’t mean you automatically get a threesome. Don’t be a perv.” “Why does everyone keep saying that?” he mumbled to himself.

That night while Sam slept, Dean’s hand crept between Holly’s legs, fingers slipping into her panties. He didn’t get far before her hand gripped his wrist. He snuggled closer into her back and whispered, “Please?” She shook her head. “He won’t hear if you’re quiet. He’s out cold” he said, sliding his fingers into her folds. “No” she whispered and shifted to her back pulling his hand free. “I’m super horny though” he whined. “You’re always super horny” she laughed and shoved his shoulder. “Car?” he suggested, sticking his bottom lip out. She couldn’t resist him when he pouted like that and nodded, “Car.” 

It was pouring out, which meant the likelihood of being seen or heard was slim, not that anyone in this seedy motel would care. She quickly pulled off her sleep shorts and panties as Dean yanked down his sweats, letting his monster spring free and leaving him naked. “There’s my big, bad boy” she grinned and slid to her knees on the floor of the car. She licked the dewy drop from the tip, making him hiss in anticipation. “How long has it been since you’ve come?” she asked looking up at him. He was watching her intently. He was beautiful, rain pounding loud on the car which blurred everything else around them. “Since you made me come” he stroked her hair, “I only come with you.” Her eyebrows shot up, “Dean. That was more than a week ago! What are you doing in those long showers?” He shrugged, “I mean, I still play with it, but I just don’t let myself finish. I’ve gotta hustle more pool so we can spring for our own room more often.” 

She was stroking him gently as he spoke, occasionally flicking her tongue out to lick him. “That explains the epic boner you had me hide in the nursing home tonight” she laughed and sucked his head into her mouth. “Fuck! Yeah, was either fuck you right there in front of Sam or take a nap. Shit, baby, you’re mouth is like silk” he moaned, head dropping back against the back of the seat. She let him out with a loud pop, “Do you want to come before I ride your cock? I think you’ve got two in you tonight.” He nodded vigorously, eyes back on her, “Yeah, I think I’ve got two in me. Especially if you tell me about your sexy times with Josie.” “Perv” she said stifling a laugh by stuffing his cock in her mouth. “Fucking hell” he sighed and she moaned around him. 

Dean cradled her head in his large hands, letting her work at her own pace. Her silky hair falling over his arms and thighs sent delicious shivers through him. He wasn’t going to last long if she kept up with that magical tongue of hers. “Baby, I’m gonna lose it real soon if you…fuck…if you keep doing that” he warned. She pulled him from her mouth, saliva dripping her lips and onto his cock, “I thought you wanted to come in my mouth.” Holy fuck she was the sexiest woman he’d ever known. “Yeah, you’re right” he said laughing and tilted her head back down. She slurped him back in, her small hands gripping his thighs tightly, feeling him tense up as she edged him into her throat. “Yessss, like that, let me fuck your throat” he groaned and she held still giving his legs a squeeze so he knew she was ready. He held her head still and lifted his hips and slid himself into her tight throat, groaning and dropping his head back. He gently fucked into her a few thrusts before backing off so she could suck in a breath. She squeezed his legs again telling him to go and he did. This rhythm was repeated until she cupped his balls in her hand, twirling them gently. “FUCK! Fuck, hold still baby” he warned and he backed himself up and spilled onto her tongue. She latched onto him sucking up every drop, massaging his balls as he shook and shouted her name. 

When he finished, she made sure he was watching her when she swallowed it down. “Perv” he teased and let his hands fall to his sides. Giggling she climbed up onto his lap, looping her arms around his neck. “Like that?” she asked. “No. I fucking loved that. I swear, every time you touch me is better than the last” he sighed contentedly. She reached for his phone and pulled up his music app. When she found what she was looking for she pressed play and dropped it on the seat, filling the car with Doja Cat’s Freak. He looked over and read the playlist title “Songs To Strip To. Nice.” She nodded and started moving her hips, moving her pussy over his still half-hard cock, “Keep your hands to yourself, sir.” “Oh, I’m gonna want a true lap-dance from you soon. I’ll make sure I’ve got plenty of cash” he grinned. She danced on his lap through the song and into the next then pulled her shirt off. “You are fucking perfect” he crooned, his eyes soaking up every inch of her as she leaned back, slowly grinding his now very hard cock. 

He wanted to touch her, to run his hands all over her, but saw how into it she was, so he kept his hands safely on her knees. He watched her breathing become lightly ragged. She lifted up pulled his cock out from under her, sliding him between her wet lips and settled back into a grinding dance, using him to rub against her clit. “Fuck baby, you’re about to come aren’t you?” he growled. She nodded and leaned forward brushing her nipples against his chest. Her hips picked up speed and there was no longer any pretense of dancing. She was straight up chasing her orgasm, grinding on his length and he’d never seen anything hotter in his life. She destroyed any chance he’d ever enjoy a strip club again. Not when he knew this was waiting for him. He made a note to install a stripper pole somewhere in the bunker. “Fuck, Dean!” she shouted and gripped his shoulders tight as she came hard, body shaking over him. She finally fell against him and his arms immediately wrapped around her, stroking her back as she calmed down. “I’m the luckiest man alive” he murmured. “That was just a warmup. Want some Champagne Room extras?” she whispered in his ear, licking the shell. “Baby, what you just did was most definitely straight from the extras menu, but hell yeah. I want everything you’ve got” he groaned. 

She leaned back again, resting her shoulders on the back of the front seat, eyes closed. “Wanna put it in me? Is that what you want?” she asked, rolling her hips. “Yes” he said, eyes locked on her dripping pussy. “What’s it worth to you?” she asked. “Anything you want. Absolutely anything, baby” he promised. “Hmmm…I want two things” a slow smile spreading over her face. “Anything, please baby, let me slide it in” he pleaded. “First, I want to drive Baby” her grin wide now. “Oh, uh…okay, sure, I’ll teach you how to handle her” he nodded now reaching down and gasping himself. “And I want you to tie me down and fuck me” she said, groaning on the last two words as his fingers grazed her clit. “That’s not hardship, baby. I’ll gladly do that” he said. “But, I want more than just being tied down. I want you to use me. Hard. Make me beg for you” she was panting now. “Damn it baby. Yes, we’re doing that” he promised. “You don’t understand” she said, running her hands over her breasts. “When I say hard…oh fuck…I want to feel you for days after. Spank me. Smack my pussy. Rough me up. Leave marks on me. Do you understand?” she asked as her hand slipped down to her pussy where she rolled her clit in her fingers. “I’ll do anything you want. Anything to make you come, baby” his hands were gripping her hips harder than he ever had before. She was likely going to have bruises and she loved it. 

“Put it in me, baby. Now” she sighed, eyes still closed. Dean gripped his cock and lined it up with her pussy, slipping the head in, feeling her open up for him. She rolled her hips once, letting him slide in deep and kept rolling in time to the music. “Tell me about her” he asked. “Oh Dean, she tastes like tart honey. Delicious” she moaned. “More” he encouraged watching as she fucked herself on him was mesmerizing. “Sometimes we would finger each other while riding back to the motel after a hunt. Too fucking hot to wait. She once ate my pussy on the hood of the car with dead vamps all over the ground” her words coming in short gasps. “Fuck. She make you come hard?” he asked. “Always” she moaned, “Dean…fuck, Dean.” His hands were now roaming her body, pinching her nipples. “We’ve never had a threesome, but we have seen each other fucking before. She brought a guys back to our room and fucked them, watching each other” she was fucking him fast now and reached out for his hands. He grabbed them and helped her up. Her hair fell around his shoulders as she leaned forward, her forehead pressing against his watching his eyes flare. “I don’t like hearing about another man fucking you” he growled. “But you’re picturing yourself in that position, aren’t you? Thinking about fucking me hard while she watches” she could barely get the words out now. “Fuck yes, baby come for me. Damn it, come for me!” he shouted and she did, hard and long, taking him with her. 

They sat in silence, feeling their bodies quiver gently as they calmed. Holly’s pussy still spasming lightly around Dean’s cock. He pressed his lips to hers and she sighed, dragging her tired arms up his arms to wrap her hands around his neck, thumbs stroking over his skin. “She’s already asked about you. Wanting to know how serious we are. Wanting to know if I’m still available to play. I don’t want to share you, Dean” she confessed. “Baby, I’m 100% yours and at your complete mercy. I’ll stop talking about it if you want” he promised. “It’s not that. I mean, this was really hot. I just…I don’t want to share you with her. I don’t want to see you touch her” she said. Dean saw the tears in her eyes and sat up straighter. “It won’t happen. You are my dream, baby. You are my perfect woman. I don’t tell you enough because, you know me and feelings” he shrugged. “Feelings are weird. I know” she laughed. “Yeah. But really, baby, I won’t push the issue. You are too important to me to risk losing you. Do you understand?” he asked. She nodded. “I’m really alright with talking about it, though. Doing what we just did. It was fun” she smiled. “Damn fun and I’m putting in a stripper pole. Dungeon maybe?” he suggested, raising his eyebrows. “Gym makes more sense, but who says we have to have just one?” she asked. “Damn it, you are the perfect fucking woman” he shouted and nipped her shoulder in his teeth. “Come on. Let’s get back inside. I need a couple hours sleep or it’ll be a miserable ride home for you and Sammy” she said. They dressed and ran through the rain, slipping quietly into the room and back into bed. Dean held her close, wondering as he fell asleep how he managed to get so lucky finding her. 


	3. Besties Reunited

**Summary for the Chapter:**

> Holly is reunited with her BFF Josie.

“OH MAH GAH!” they screamed in unison and threw themselves at each other, falling to the ground. Sam and Dean stood there with amused expressions as the girls sat on the hard ground, legs tangled as they spoke quickly and at the same time holding two entirely different conversations without missing a beat. “It’s weird” Dean said. “So weird” Sam agreed. “It’s kinda like that Gilmore Girls show you watch in secret” Dean said earning himself a quality Sam bitchface. 

Eventually the women remembered they weren’t alone and climbed to their feet. They were almost complete opposites, physically. Holly a curvy, busty, brunette with loose ringlets floating around her shoulders and crystal blue eyes; Josie a slim, small chested blonde with straight hair grazing her shoulders and dark brown eyes, though both had trouble scraping 5’3”. “Josie, I’d love for you to meet Sam and Dean Winchester” Holly smiled broadly. “Hi, I’m Sam” he said extending his hand, “It’s great to meet you.” She smiled warmly, “You too. And you must be Dean.” Turning, she gave him a long once over and he finally asked, “Did I pass muster?” “Lemme see your butt” she waved her hand in a circular motion. Dean’s mouth fell open, then snapped shut looking at Holly for help. Holly only shrugged and mimicked the turn around motion with her own finger. Sam laughed loudly as Dean sighed and complied. “Nice pick, though I’d have gone for the big one” she teased and hooked her arm into Holly’s. “So, let’s see the Batcave” she said and thanked Sam for picking up her bag. “Dude, I’m big. I’m 6’1” and I kill things, that’s big” he whined quietly to Sam. “Yeah, but I’ll always be the big one, big brother” he laughed and followed the girls into the bunker.

Holly toured Josie around the bunker and showed her to her room, flopping on her bed and watching her unpack. “So, you and Dean. Scoop me” Josie said. “He…he makes me feel amazing. My whole body lights up when he walks into a room. He makes me laugh” Holly gushed. “And the sex?” she asked dropping her panties in the top drawer. “Holy fuckballs! I come so fucking hard and so often. I never knew a cock could feel so good and I’ve had plenty. And his hands are so big and strong and gentle” she sighed. “Kinks?” Josie asked. “He’s into everything and is willing to try anything at least once but doesn’t pressure me. I recently asked him to do that thing I’ve been wanting to try, where I get tied up and used. He’s up for it, but is worried about my wanting him to be rough enough to leave marks on me. He’s afraid he’ll hurt me” she said. Josie nodded, “I am glad to hear he’s nervous about it. I’m very glad you’re happy, baby girl. I’ve been missing you, but I’m glad you’re happy.” “Josie, I want to, but I won’t cheat on him and I can’t share him. I’m finding myself incredibly jealous of the idea. Him touching someone else? No, not happening” she said. Josie laid next to her on the bed, “I get it and I’m fine. I mean, my kitty hasn’t been eaten properly since you last did it, but I’ll survive. You’re my best friend and I love you.” Holly sighed in relief, “Love you, too, bestie. Come on, the boys are making dinner.” 

Laughing as they entered the kitchen Dean looked up from the grill pan. “Please tell me you’re a meat eater” he said to Josie. “I am, thanks. I’m mostly a healthy eater, but whatever your making smells like heaven and I make an exception when someone else is doing the cooking and whenever there is bacon” she smiled. Sam appeared from the other side of the fridge door, “I’m a healthy eater too, unless he’s making dinner. Feel free to help yourself to whatever you find.” She nodded, “Thanks. Okay, put me to work. I’m not a chef, but all hunters can handle basic knifework.” Sam set her to chopping vegetables for the salad and got to work on the dressing. She watched him dumping a ton of herbs into a blender. “What’s that gonna be?” she asked. “Green Goddess dressing. It’s the only way I can get Dean to eat a salad” he shrugged. 

“Salad is what my food eats” Dean said and placed the burgers in the cast iron skillet he’d just fried the bacon in. Holly was cutting and squeezing limes and when Josie saw the bottle of tequila on the counter she said, “Oh shit. Gonna start me off with truth serum and a hangover?” Holly laughed, “Duh!” “Truth serum?” Sam asked. “Oh yeah, when she drinks margaritas she drops truth bombs all over the place” Holly said excitedly. “I’m pretty direct as it is. Truth serum is a bad idea for me in general” Josie sighed. “I’m compiling a list of questions in my head right now” Dean said from the stove. “Don’t be a perv” Holly and Sam said in unison. 

“I can’t eat another bite!” Holly shouted and pushed her plate away. “That’s the best burger I’ve ever had or will ever likely have. And I’ve had two doses of truth serum, remember” Josie said. Beaming Dean picked up their plates and walked them to the sink. “Dressing was stellar too” she said to Sam. “Thanks, but keep that on the down low, I think you just complimented him into doing the dishes” he laughed. “Come on, let’s go chill in the library. I’ll bring the fresh pitcher so grab your glass” Holly said to Josie.

“This place is fantastic. An underground lair. So cool” she sighed looking over the titles on one of the bookcases. “Have you digitalized this?” she asked Sam as he came into the room. “We have, well, Holly and I have. Dean’s way of helping was to avoid it entirely” he said. “I’m not the best with tech either. I can barely use my phone half the time. I’m the youngest and hottest old man you’ll ever meet” she laughed and settled into a chair next to Holly. 

Sometime between drinks three and four Josie had them all in hysterics as she told them how Holly lost a bet and had to work a case without lying to anyone. “She leaned over the counter and pushed her boobs together like this, oh shit, I can’t show you cuz I don’t have any boobs, but she pushed them together and said to the guy, ‘But sir, I really need to know where he lives. I have something I need to show him.’ Then she looked down at her boobs and touched them. I swear she just about felt herself up. I threw up in my mouth a little and was also super turned on. I was in a weird place for days after that. So, we get to the guy’s house and I’m like, ‘You have to show the shifter your boobs. If you don’t, you lied to the postal worker and that’s against the rules.” Dean was laughing so hard, tears were streaming down his face. “Holly walked up the door and when he answers, she pulls up her shirt flashing him and then I cut his head off” she finished and downed the rest of her drink. Sam was able to speak first, “That is the best hunting story I’ve ever heard!” 

“Okay, enough of that!” Josie said, wiping the tears from her face. Josie shrugged, “Hey, Dean asked for my funniest hunting story about you.” “Oh, shit,” Dean said, “You delivered.” “I’m making another pitcher. Dean, come cut the limes, I’m a little buzzed” she said. “Sure, baby” he said and followed her. “I think I like him, but I’ll tell you what I plan on telling him when I get him alone. He fucks her over or hurts her, I’ll do him like the shifter I just told you about” she said sitting back in her chair. “Pretty much exactly what I told him when they started up, so, I’ll flash him my boobs and can cut his head off” Sam said making Josie howl with laughter.

“Shit, I’m the only one to get her laughing like that!” Josie said sliding up and wrapping her arm around Dean at the kitchen counter. “I think Sam’s interested and he is never interested in anyone” Dean said dropping a kiss on her head. “Sam and Josie. Huh. Hadn’t considered that” she said quietly and walked away for the tequila. “You okay with that, baby? It’d be kinda normal if it was weird for you seeing your ex with someone else” he said. “Oh, she’s not my ex. We are best friends who sometimes enjoyed each other. That’s it. She’s got truth serum in her, so feel free to ask her about it” she said. “I know you and I know us. We’re solid, baby. Just promise me, if you ever want to be with her, talk to me first. I’m sure we can work something out.” She sighed, “Perv.” 

They reappeared in the library and Dean asked, “What’s so funny out here?” Sam pushed his and Josie’s glasses towards Dean for refills, “Oh, we were just talking about how if you displease Holly in any way, I’m gonna flash my boobs so Josie can cut your head off.” The two of them lost it again leaving Holly giggling across the table from an open-mouthed Dean. He grumbled, “Okay, let’s switch it up a bit. I found a game. Hang on.” They watched him struggle to find it on his phone and Holly finally took it from him and a few seconds later she said “Would You Rather – Dirty Edition?” He smiled, “Yep!” “I’m in!” Josie said raising her glass. “Me too!” Sam said clinking with her. Dean looked over at Holly with an “I told you so look.” Holly asked, “Who goes first?” Sam said, “Most vamps killed in a night goes first.” “Ooh, good one. My best is 7, but I’m looking to improve” Holly said. “I’m at 9, Dean is 6” Sam said. “NO! I’m at 14 and you know it!” Sam shook his head, “No. Cas killed 14.” Dean threw his hands in the air, “Who called Cas? ME!” Holly sighed, “No, Dean. That’s Castiel’s count, not yours. I’m only at 4, boo!” 

“Okay Sam: Would you rather work recycling human poop for the rest of your life OR work with dangerous or explosive chemicals for the rest of your life?” Holly asked. “OOOOH! Sam the germ freak faces off against Sam the anything with chemicals will kill you freak!” Dean just about squealed. Holly giggled and nodded, “It’ll be a good showdown, I think.” Sam sat back grimacing as he thought it over. “Well, poop is full of nasty stuff, but I saw an episode of Dirty Jobs on Discovery where they actually do this. It gets funneled out of the water and okay, you don’t wanna hear that…I’m gonna go with poop over chemicals. Yep. Definitely.” Dean made obnoxious gagging noises as Holly moved on. “Josie: Would you rather have your thoughts broadcast so everyone could hear them as you were thinking them OR would you rather never be allowed to wear clothes again but keep your thoughts to yourself?” Holly asked. “Hmmm. My thoughts are pretty fucked up and everyone hearing them would make hunting impossible. So, I guess I’d be a naked hunter” she nodded. “My turn: Would I rather fight Jackie Chan or Jet Li?” she said. “Hey! I want that one!” Dean said. “Nope. It’s my turn, I’m next to Josie” she said swatting Dean’s hand away from the phone. “I’d fight Jackie Chan cuz I feel like we could go get a beer and hang out after” she said. “Laaaaaame!” Dean said. “Obviously you fight Jet Li so you can a) say you fought Jet Li and b) learn some fight moves from Jet Li!” Dean said throwing an arm out towards Sam for backup. “Sorry, Holly, gotta go with Dean on this one” he said. “Fine. Dean: Would you rather be a character in Lord of the Rings or Harry Potter?” she giggled at that one. “Well, I’m good on a quest and super loyal and I already have my own Sam. But then again, I would have slayed Voldemort in the beginning and saved everyone a lot of trouble, but I’d also wind up hunting all the witches cuz, you know I hate witches. Except that Hermione one reminds me of you” he said winking at Holly. He threw his head back a minute and came up saying, “Lord of the Rings. I’d totally bang all the lady elves.” 

They continued until the pitcher was emptied, refilled and emptied again. Watching Holly and Dean stumble to bed, Sam asked, “Know your way?” “I left a trail of breadcrumbs” Josie smiled. Sam followed her anyway and from the doorway said “There are extra pillows and blankets in the closet and a robe if you need one. Showers get complicated, just one big shower room. And Dean and Holly are forever having shower sex, so, check before you go in. Oh, and noise carries down the hall. If you have noise canceling earphones, use them. They get loud when they drink. Well, louder than they do when they don’t drink, which is still pretty loud” he laughed. As if on cue, Holly’s deep and long moan floated down the hall. “See?” he smirked. “I’m three doors down on the left, if you need anything” he said and grabbed her doorknob. “Thanks, Sam. Goodnight” she smiled, finding herself unusually quiet. He nodded and closed the door with a soft click. 

Josie undressed and stumbled into bed, listening to the familiar sounds of her best friend’s passion. Not one to ignore a freebie, she slipped her hand down her body, cupping her sex, which was already wet. She quickly got herself up to where Holly seemed to be and sped up as Holly’s moans changed to shouting Dean’s name. She’d love to be there watching them, but found her thoughts drifting to Sam. Was he listening? Doing what she’s doing now? Fuck that could be hot. Getting off with each other while listening to the racket coming from down the hall. She found herself coming hard and fast. “Shit” she whispered hoping Sam didn’t hear her own cry as her orgasm rocked through her. 

-

“Good morning” Sam said shuffling into the kitchen in his sweats, hair still lightly mussed from bed. “Hi. Coffee is on. I’m making breakfast. How upset will Dean be without breakfast meat?” she asked. “Very” he said over his shoulder as he poured out coffee. “Okay. I’m going to make a frittata. Cool if I use your Beyond Sausage?” she asked. “Cool with me, just don’t let him see the package” he warned smirking at her boldness when she held her finger up to her lips, “Shhh.” He sat at the table and watched her cook. She quickly fried up the sausage with onion and peppers, beat the eggs, shredded swiss cheese and minced fresh herbs. She dug around in the fridge and came out with some cherry tomatoes. She threw it all together and set it to bake in the oven. Refilling her coffee she joined Sam at the table. 

“Bed was super comfortable” she said, feeling the need to fill the silence. “Oh, Dean insisted we swap out the mattresses for memory foam. He wasn’t wrong. Makes for great sleep, especially after a rough hunt” he said. “Get a lot of visitors here?” she asked. “We’ve got two roommates who are in and out. Jack and Castiel. Hopefully you’ll meet them while you’re here. They are out doing whatever they do” he laughed and sipped his coffee. “We sometimes have groups of hunters here when working on a big, coordinated hunt, but mostly it’s just the three of us” he said. “How did you find this place?” she asked. Sam explained the Men of Letters and how they were legacies by birth. “Pretty amazing. I’d love to check out some of your books. If you don’t mind” she said. He nodded, “Help yourself. Just make sure you put them back where you found them or Holly will lose her mind. She’s got a system and even I won’t mess with it.”

-

“Baby, I’m so sleepy” Holly murmured as Dean kissed her shoulder. “Mmm. Me too” he said pressing his cock against her ass. “That doesn’t feel sleepy” she said stuffing her face further into the pillow. “You don’t have to do anything baby, except ask me to fuck you” he moved his lips to her neck. She moaned his name as his hand found her pussy, gently stroking. “You’re dripping wet” he groaned, dipping his fingers into her. She lifted her leg up and draped it over his. “Tell me what you want, baby” he said. “Fuck me. Please fuck me” she asked softly. He lined himself up and slowly sunk into her. “Being inside you is indescribable” he sighed into her ear. He cupped her breast, lightly thumbing the nipple as he gently thrust in and out of her, pulling sighs of pleasure from her lips. 

It didn’t take long before her pussy tightened around him. “I love watching you come undone” he panted, quickly losing his will to hold back his own end. He rolled her onto her belly and straddled her thighs. Cupping her ass in his big hands, he opened her up and watched his cock slide in and out of her soaked pussy. “Dean, I’m, oh fuck, again” she groaned and stuffed her face into the pillow as she came again. This time he couldn’t stop it and pumped her full, sitting back on her legs until his heartbeat settled. 

He stroked her ass, accidentally tickling her. Once he discovered that, he didn’t stop until her laughing screams could be heard in the kitchen.

-

“What do you say we get out of here before they show up looking smug with their sex hair?” Josie said pulling the casserole out of the oven. “Won’t Holly be disappointed if I steal you away?” Sam asked. “She’ll be fine. Let me make some toast and we’ll turn this into sandwiches to go” she grabbed a loaf of bread. Sam got up and stuck his head out into the hall, “Sounds like they’re heading for the shower. We’ve got forty minutes to escape.” They were in Josie’s truck in ten minutes heading towards town. 

“This is incredible” Sam said around a mouthful of breakfast sandwich. “Thanks. I like to cook, just never have a kitchen to do it” she shrugged as they walked up the tree lined street with their sandwiches and shared thermos of coffee. “This is a pretty town. Especially while it’s still asleep like this” she said watching the grocer hose down his sidewalk. “I like it here. Big cities are great for art and food and culture, but I can relax here. I can breathe here” he said. “Careful. You’re dangerously close to quoting John Mellencamp” she teased. He laughed and she said, “I know what you mean, but I tend to breathe better in cities where I can disappear.” He said, “Maybe we can change your mind while you’re here.” 

They spent the morning shopping at the farmer’s market loading up on produce and fresh meats. “I love wildflower honey” she said picking up a jar and holding it up to the light, smiling as golden rays shined through. She bought the honey and some goat cheese. “Just need some crusty bread and I’m set” she said passing the bag to Sam who was serving happily as the pack mule. 

-

“Dinner!” Sam announced as they brought trays of food into the library. From their shopping hoard, they’d made grilled lemon rosemary chicken, parmesan roasted broccoli and bruschetta with goat cheese, roasted tomatoes and a honey drizzle. “Sam, if I knew you could do this, I would have made you cook more” Dean said moaning over his meal. “It was Josie. I just follow direction well” Sam said. With a mouthful of bread and cheese Dean said, “That egg thing this morning was fantastic.” She smiled, avoiding Sam’s eyes or she’d start laughing, “Thanks.” 

After dinner they decided pool was in order and headed out to the bar. “We don’t hustle in our own neighborhood” Dean warned as he chalked up. “I’ll try to hold back” Josie laughed. She and Dean got into such a heated match that Sam and Holly sat it out at the bar. “She’s only here a week or so Sam. If you’re into her, better move at twice your normal speed” she teased. “I haven’t laughed this much with anyone since Jess” he said quietly, a frown forming on his face. “She likes you a lot and before you can start with the ‘I’m a fucked-up hunter and don’t want to fuck her life up’ crap that seems to be the Winchester fall back, she’s just as fucked up. We all are, so, that’s an invalid argument” she said passing him a fresh beer. Sam pulled her into a bear hug. “What’s this for?” she squealed. “You’re great. I’m so glad Dean worked out some of his issues and got you to stick around” he smiled down at her. “HANDS OFF MY WOMAN!” Dean shouted from across the room pointing his pool cue at them with a fake angry face. Sam just hugged her harder and kissed her head. 


End file.
